I had anal sex only once in my life, and I still remember it, every detail of it, till this day.
We were graduating hs, so, legal of age, and she was the girl everyone lusted for. Tall, very beautiful, dark hair, top girl in the school. I was dating her cousin, who was also kind of hot, but not on her level. It was prom night, and, little detour here, in Europe we don't do these like in the US, prom night is for the graduates only, and you can come with another graduate as your date. So I asked her, since I knew her, we were kind of friends, and my gf, her cousin, was at the entrance of the hotel, where friends and family gather to clap and cheer for the graduate couples going into their first "grand" party of their lives.
I was all over her, all night long, dancing with her, feeling her up, and she didn't object. We drank a lot, and at the end of the evening, we all went out, to go crazy on the streets. After some time, we got to a secluded spot, and started kissing. I wanted more, but she was reluctant, she said that even this is too much, that it is a betrayal of her cousin, that she made a mistake, that she hates me since I never told her how I feel before going out with her cousin, since she was into me, for years. And that was it.
Afterwards, my gf called me, angry as hell. She confessed to her, and all hell broke loose, even some punches were exchanged, and nothing good came of it. Two month later, I moved to a city, for uni, and all I knew is that she moved to a different city.
She did text me soon after, and we renewed our contact. She obviously wanted me, but she was still reluctant, and, after almost three months of going back and forth, she invited me to come see her.
So I did. We got out, and she was wearing one of those tartan skirts, with pantyhose underneath, and we ended at her place, with her room mate in the other room, drunk and horny. We ended up on the bed, and I pulled her nylons down, and just went to town, from the spooning position.
She was ready, she was wet, she looked amazing, and, with one of the thrusts, I missed a little, and pressed against her ass. Got back in the pussy, and next time, I did it on purpose. I backed up a little, and, seemingly clumsy, tried to go back in, but I went to the place I wanted to be, slowly at first. She moaned really loud, but didn't protest, so I continued.
At that point, that was the highlight of my life, ass fucking the hottest girl from school, and the best part is, when I am drunk, I can go for days.
After few minutes, I started going faster, and deeper, and harder, and it ended up as a 20 something minute hard, anal session, while she screamed from pleasure.
We had sex three more times that weekend, and when I got back to uni, I thought I found a woman of my life. Only I didn't.
She told me she just can't do it, since her cousin, what are the odds, reached back to her, two days after I left, and she can't blow that opportunity, since they were very close.
I still think, that that wasn't the case, that my lust, and that night of anal, made her second guess me as a choice, even though she clearly enjoyed it.
And no, I never felt remorse for how it went, I would trade that one night of sex with her, for the sum of all my sexual experiences, it was that good.
